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Choose Chicago Head Osmond Steps Down

Choose Chicago board member Gamble to assume Interim CEO role during search

By Todd R. Berger

1.12.24 Choose Chicago President and CEO Lynn Osmond - Portrait
Choose Chicago President and CEO Lynn Osmond to step down Jan. 31. || Courtesy of Choose Chicago

Choose Chicago  President and CEO Lynn Osmond has decided to leave the organization effective Jan. 31 to focus her time and energies on a family health matter.

“It has been gratifying to serve as CEO of Choose Chicago for nearly two years, but, right now, I have to put my family first,” Osmond says. “I know this is the right decision for me, my family, and for the organization at this time as we gear up for a very busy year with the 2024 Democratic National Convention coming to town.”

“Choose Chicago is grateful for Lynn’s service to the organization and our city,” says Choose Chicago Board Chair Glenn Eden. “Under her leadership, the organization has made great strides and is well-positioned for the future. We thank Lynn for her dedication to ensuring Choose Chicago continues to play an important role in demonstrating everything that makes Chicago a world-class city for travelers of all kinds.”

During Osmond’s time leading the organization, the city secured and hosted major national and international events such as the 2024 Democratic National Convention and the city’s first-ever NASCAR race, generating global media exposure for the city; travel recovered from pandemic levels to achieve a projected 54.5 million visitors in 2023, resulting in an all-time record in summer hotel revenue and tax collections; and Condé Nast Traveler readers named Chicago the Best Big City in the U.S. for an unprecedented seventh consecutive year.

Chicago’s tourism and hospitality industry is on a positive path, and with a dedicated team, Choose Chicago is in a strong position to continue growing Chicago travel and tourism.

Osmond was appointed president and CEO of Choose Chicago in March 2022. Rich Gamble will act as interim CEO following Osmond’s departure.

Gamble is a recognized strategic and tactical executive leader with over 30 years of experience collaborating with high-performing teams to create and drive organizational objectives into successful outcomes.

Gamble, who currently serves on the Choose Chicago board of directors as chair of the nominating committee and as a member of the executive committee, will assume the interim role as the organization begins its search process for a CEO. More details on the search process will be released later this month.

“I am pleased to be able to provide support to the organization during this time of transition,” says Gamble. “Choose Chicago has an extraordinarily strong team with deep experience. The organization is well poised to continue to build on the momentum established in 2023.”

Most recently, Gamble provided advisory and management consulting services through Realized Value Collaborative LLC. Prior to that, he served as chief operating officer and executive vice president for six years at the Chicago Zoological Society’s Brookfield Zoo (CZS). He joined CZS following an impressive 16-year career with the Chicago Tribune where he last served as the vice president and general manager of Chicagoland Publishing and publisher of Chicago Magazine. Prior to this, Gamble served in the roles of vice president of finance and Operations, Publisher & General Manger of ¡Exito! Newspaper, Director of Business development, and director of the post-press packaging division. Before Tribune Company, Gamble held a variety of leadership roles in the quick-service restaurant and industrial supply industries.

Gamble has a strong history of service to the City of Chicago, and he has developed relationships across a variety of industries. He is currently the board chair for the Chicago Loop Alliance and past board chair of the Magnificent Mile Association.


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